Hydrochloric Acid → HCID 14674164, compound

HRID 1614210Notes

Reaction equation

HRID 1614210 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:14]=[CH:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=1)=[O:4].[ClH:15].[N+:16]([C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[O:22][CH:23]1[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]1)([O-:18])=[O:17].C(N(CC)CC)C.Cl>C(O)C>[ClH:15].[N+:16]([C:19]1[CH:20]=[C:21]([CH:29]=[CH:30][CH:31]=1)[O:22][CH:23]1[CH2:24][CH2:25][N:26]([CH2:2][C:3]([C:5]2[CH:14]=[CH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[CH:6]=2)=[O:4])[CH2:27][CH2:28]1)([O-:18])=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 691792-Bromo-2'-acetonaphthoneHCID 224033414-(3-Nitrophenoxy)piperidine--hydrogen chloride (1/1)

Product 1

HCID 14674164HCID 14674164, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.63 g of 2-bromo-2'-acetonaphthone, 0.65 g of 4-(m-nitrophenoxy)piperidine hydrochloride, and 1 g of triethylamine were added to 100 ml of ethanol. The mixture was refluxed for 30 min. The solvent was distilled off, and dichloromethane was added to the residue. The mixture was washed with water and dried. The dichloromethane was distilled off, and the residue was purified by column chromatography (silica gel) to prepare an oleaginous intended compound. The compound was converted into a hydrochloride by an ordinary method and then recrystallized to prepare 0.15 g of an intended hydrochloride.

Workup

  1. temperatureThe mixture was refluxed for 30 min
  2. distillationThe solvent was distilled off
  3. additiondichloromethane was added to the residue
  4. washThe mixture was washed with water
  5. customdried
  6. distillationThe dichloromethane was distilled off
  7. customthe residue was purified by column chromatography (silica gel)
  8. customto prepare an oleaginous intended compound
  9. customrecrystallized
  10. customto prepare 0.15 g of an intended hydrochloride

Sources & evidence

ORD record
ord-0036256189be44d4a9a75fe69f54fd79
Source dataset
uspto-grants-1993_03
Patent number
US05196439

Reaction notes

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